Methanol → HCID 67281011, compound

HRID 515489Notes

Reaction equation

HRID 515489 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][N:8]2[CH2:14][CH2:13][CH2:12][O:11][CH:10]([CH3:15])[C:9]2=O)=[CH:5][CH:4]=1.CO.[OH-].[Na+]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[CH2:14][CH2:13][CH2:12][O:11][CH:10]([CH3:15])[CH2:9]2)=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 66718654HCID 66718654, compound

Product 1

HCID 67281011HCID 67281011, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-(4-methoxy-benzyl)-2-methyl-[1,4]oxazepan-3-one (2.00 g, 8.02 mmol) in tetrahydrofuran (24 ml) was added 1M borane-tetrahydrofuran complex in tetrahydrofuran (27.3 ml, 27.3 mmol) at 0° C. The mixture was stirred at room temperature for 3 hours. After cooling to 0° C., methanol (20 ml) and 6N sodium hydroxide (20 ml) was added carefully. The resulting mixture was refluxed for 2 hours and cooled to room temperature. The solvent was removed under reduced pressure. The residue was partitioned between saturated ammonium chloride solution and ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography (eluant: hexane/ethyl acetate=1/1) to afford 4-(4-methoxybenzyl)-2-methyl-[1,4]oxazepane as colorless oil (1.66 g, 88%).

Workup

  1. temperatureAfter cooling to 0° C.
  2. temperatureThe resulting mixture was refluxed for 2 hours
  3. temperaturecooled to room temperature
  4. customThe solvent was removed under reduced pressure
  5. customThe residue was partitioned between saturated ammonium chloride solution and ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by silica gel column chromatography (eluant: hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-6b08a3eb1700444b906d31a286ca3d4a
Source dataset
uspto-grants-2015_08
Patent number
US09108957B2

Reaction notes

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